Chemistry of renieramycins. Part 5. Structure elucidation of renieramycin-type derivatives O, Q, R, and S from Thai marine sponge Xestospongia species pretreated with potassium cyanide

Journal of Natural Products

Volumn 67, Issue 6, 2004, Pages 1023-1028

  Amnuoypol, Surattana ^a   Suwanborirux, Khanit ^a   Pummangura, Sunibhond ^a   Kubo, Akinori ^b   Tanaka, Chieko ^b   Saito, Naoki ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; POTASSIUM CYANIDE; RENIERAMYCIN DERIVATIVE; RENIERAMYCIN M; RENIERAMYCIN N; RENIERAMYCIN O; RENIERAMYCIN Q; RENIERAMYCIN R; RENIERAMYCIN S; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ASSAY; CHEMICAL REACTION; COELENTERATE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; IC 50; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; THAILAND; XESTOSPONGIA;

ACETYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; TETRAHYDROISOQUINOLINES; TUMOR CELLS, CULTURED;

COELENTERATA; XESTOSPONGIA;

EID: 3042675982     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030534o     Document Type: Article

References (23)

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22. 1H NMR spectrum of 7, the diagnostic homoallylic coupling (ca. 3 Hz) between 1-H (δ 4.13 ppm) and 4-Hβ (δ 1.66 ppm) through five bonds was negligible, and this phenomenon revealed that this compound might have retained the hydroquinone moiety at ring A. Additional evidence was provided by HMBC experiments. See Experimental Section.
23. The direct conversion of 1m into 6 by reductive acetylation using zinc powder and acetic anhydride failed. In contrast, acetylation of 5 with acetic anhydride and acetic acid (4:1 w/w) at 100 °C for 1 h afforded 6 in low yield (15%, 2 steps).